You Should Ask More Questions: Here Are 5 Ways to Get Started

My young sons ask a million questions. It is impressive, this seemingly never ending flow, like an irrepressible river. Their questions respond to the deluge of complex information in our bewildering world, and their developing minds deposit answers in a fertile delta that allows them to grow.

Questions are the gateway to meaning for children. In fact, kids ask around 300 questions a day when they are about 6. When they run out of legitimate questions, they generate even perplexing ones, like the one I recently was asked: “what if you bunted a baseball and it went in the air all the way to South America?” When they run out of things to make meaning from, they default to questions.

Who knows why we stop asking questions as we get older. Somehow we seek to provide more answers than questions.

More often than not the answers we come up with as adults are just assumptions. We think assumptions are superior to questions.

For the last 3 years I have worked as a consultant, a profession that centers on quickly providing solutions to complex problems. I always viewed Sherlock Holmes as the ideal consultant. He swoops in to the aftermath of a chaotic problem, notices every detail, musters forth significant intuition, and works out great mysteries in his mind.

Sherlock seems to pull his solutions out of thin air. He has all the answers, and – intriguingly –  not many questions. [1] People are left in reverential awe in his wake.

But Sherlock is fiction. I can attest that, having worked as a consultant and spent time around consultants of all levels of experience and effectiveness, great consultants differ from mediocre ones in at least one respect: great consultants ask a high number of high quality questions in order to solve problems. In that sense, they are almost childlike.

So we can conclude that an important key to great consulting (or great problem solving in general) is: less Sherlock, more inner child.

How do you master the art of questions that you and I started giving up at around the age of 8? We can look at a few different walks of life where questions are successfully used and apply those strategies to our daily life.

Here are 5 strategies for introducing more questions to your daily life. Try some of these examples – perhaps with clients, your team, even your friends and family – and you will be impressed by what they do for you.

1. Uncover the Emotions Behind the Problem

People can’t make meaning without emotions, and emotions are so complicated that often people don’t consider them fully when trying to understand problems.  As a result, they don’t fully get to the meaning of problems they face or how to solve them. Asking questions that get at emotions about a problem can help surface possible solutions.

Of course, asking “how do you feel about….” can be a weirdly conspicuous experience. A good example of how to get at them more naturally comes from any televised sporting event. Here’s one: after Superbowl 50, ESPN analyst Tracy Wolfson asked Peyton Manning, “Your second superbowl [win]…What does that mean [to you]?”

His response? “I feel very grateful.” He carried this to the rest of the interview, talking about his desire to share the moment with his family. By pointing him to meaning, the interviewer guided Manning to his priority.

Other great questions that introduce emotion – and you hear our media ask them often – include “what was it like to….?” And “what stirred in you when…?” Plug the business challenges your team is experiencing into those questions, and you set the stage for revealing significant insight to begin the process of defining priorities and solutions.

2. Ask Open-Ended Questions

Often in business settings, professionals want to be agreeable, which means answering minor questions with the answer they perceive others to want them to have. People are inclined to be honest, but when presented with yes-or-no questions they often default to what they perceive to be the most frictionless response. To get around this, ask open-ended questions.

One excellent way to turn any question into an open-ended one is to use the phrase, “to what extent.” So instead of, “were you successful in your role in the product launch?” you could ask, “to what extent were you successful in your role?” [2]

3. Go Deep with Follow Up Questions

Author and talent recruitment expert Geoff Smart illustrates the power of follow up questions by advocating the use of only 4 scripted questions to screen job applicants. [3]

• What are your career goals?
• What are you really good at professionally?
• What are you not good at or not interested in professionally?
• Who were your last 5 bosses, and how will they rate your performance on a scale of 1-10 when we talk to them?

There are only four because there are so many follow up questions that naturally come into the conversation. He advocates “getting curious” by asking follow up questions that start with what or how or tell me more about… Doing so reveals so much meaning for recruiters, positioning them to make smarter hiring decisions (solving the problem of an open position successfully).

4. Start – and Finish – with Why

From the realm of operations process improvement, a great tool is the 5 Why Exercise. This approach starts by looking at a process problem and asking, “why did that happen?” And to the response, asking, “And why did that happen?” By the time the question has been asked five times, the root cause has been identified. This has been popularized in Kaizen, a proven methodology for removing waste from business processes and improving overall quality.

5. Establish Contrast

Storytelling and presentation design guru Nancy Duarte emphasizes how important contrast is to understanding [4]:

 “People are naturally drawn to contrast because life is surrounded by it. Day and night. Male and female. Up and down. Good and evil. Love and hate.”

Contrast has the dual effect of making you more interested in the listener, and helping the listener come alive and better articulate what is happening.

But the main value of contrast comes in when seeking to establish the solution. As Duarte says, “the gap between what is and what could be is established through creating contrast.”

One of my favorite questions to help create contrast, which I borrow shamelessly from Steve Blank [5], is

if you could wave a magic wand and change this situation, what would it look like?

Other great questions to use are, “five years from now, what should this look like?” or, “if this were made into a movie, what would we want to see?”

Bonus Tip: Show Some Empathy

Maybe by now you are excited to infuse your conversations with more questions. Be careful not to make people feel like they are a part of an inquisition by peppering them with question after question. Instead, share how you identify with them when they express how situations have impacted them, and especially how they’ve contributed to situations that are problematic. A simple “that must have been frustrating,” or “I’ve made that mistake before,” makes people know that you are with them, and not judging them. This encourages them to participate with you more fully in solving the problem at hand.

Asking great questions truly is an art. We started our lives asking thousands of them, and dusting off and developing this natural talent that we all possess is worth it. Developing this skill helps us establish situational meaning and solve problems more effectively for our customers, our business colleagues, our friends and our families.

[1] For a great example, check out the digital rendering of A Study in Scarlet. The questions Sherlock asks are almost exclusively rhetorical and often about how smart he is, eg, “No doubt you see the significance of this discovery of mine?”

[2] From The Evaluation Interview, by Richard A. Fear and Robert J. Chiron, 4th Edition.

[3] From Who: The A Method for Hiring, by Geoff Smart and Randy Street.

[4] This quote and the one following are from Duarte’s excellent book, Resonate.

[5] From The Startup Owner’s Manual, by Steve Blank and Bod Dorf.

Header Image credit: "Question Mark Block" by Jared Cherup, https://flic.kr/p/fhRZKU.  Licensed under creative commons